HCID 67632192, compound → 189811-07-2

HRID 54273Notes

Reaction equation

HRID 54273 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:25])([CH3:24])[CH:9]=[CH:10][Sn](CCCC)(CCCC)CCCC)=[CH:4][CH:3]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(OC(=O)C)(=O)C.CCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:25])([CH3:24])[C:9]#[CH:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67632192HCID 67632192, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 21467990189811-07-2Yield 72.4%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8003PentaneSolvent

Procedure

A mixture of 4.0 grams (0.0085 mole) of 3-(4-chlorophenyl)-3-methyl-1-tributylstannyl-1-butene and 4.3 grams (0.0096 mole) of lead tetraacetate in 30 mL of anhydrous acetic anhydride is stirred at ambient temperature for about 18 hours. After this time, the reaction mixture is diluted to 100 mL with pentane. The mixture was then filtered through a pad of diatomaceous earth. The pad of diatomaceous earth is washed with about 300 mL of pentane. The wash and the filtrate are combined and concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel, using petroleum ether as the eluant. The product-containing fractions are combined and concentrated under reduced pressure, yielding about 1.1 grams of 3-(4-chlorophenyl)-3-methyl-1-butyne. The NMR spectrum is consistent with the proposed structure.

Workup

  1. filtrationThe mixture was then filtered through a pad of diatomaceous earth
  2. washThe pad of diatomaceous earth is washed with about 300 mL of pentane
  3. washThe wash
  4. concentrationconcentrated under reduced pressure to a residue
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea05a5bb1b0c47beb44a05ef33b36035
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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